Sodium Carbonate → 4-Methyl-3-[4-(5-pyrimidinyl)pyrimidin-2-ylamino]aniline

HRID 2368778Notes

Reaction equation

HRID 2368778 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[NH:11][C:12]1[N:17]=[C:16]([C:18]2[CH:19]=[N:20][CH:21]=[N:22][CH:23]=2)[CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl>[N:13]1[CH:14]=[CH:15][C:16]([C:18]2[CH:19]=[N:20][CH:21]=[N:22][CH:23]=2)=[N:17][C:12]=1[NH:11][C:3]1[CH:4]=[C:5]([NH2:8])[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 23073521N-(2-Methyl-5-nitrophenyl)-4,5'-bipyrimidine-2-amine

Product 1

HCID 231458394-Methyl-3-[4-(5-pyrimidinyl)pyrimidin-2-ylamino]aniline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Stannous chloride dihydrate (3.6 g, 16 mmol) was dissolved in 10 mL of concentrated hydrochloric acid. The solution was added to N-(2-methyl-5-nitrophenyl)-4,5′-bipyrimidin-2-amine with violent stirring. The mixture was poured into ice-cold water after being stirred for 2 hours. It was then neutralized to pH>8 with sodium carbonate and extracted with ethyl acetate for 4 times. The pooled extracts were washed with brine, dried over magnesium sulfate and finally concentrated under reduced pressure to obtain 0.7 g of the title compound. MS (M+1)=279.13.

Workup

  1. additionThe mixture was poured into ice-cold water
  2. extractionextracted with ethyl acetate for 4 times
  3. washThe pooled extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationfinally concentrated under reduced pressure

Sources & evidence

ORD record
ord-4d05bc75ea3e4d70b15dfcca58d37b4e
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

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